Michael Ian Black is one of those self-loathing comedians you’ve heard so much about. His on-stage persona covers a wide spectrum of comic neurosis, deftly swinging between know-it-all-ism to blistering self-hatred, sometimes within the span of a single joke. He is a veteran of stage, television, and film, having performed or written some of the most memorable comedy of the last 20 years, including Michael and Michael Have Issues, Stella, and The State. And yet to hear him talk, one would think he’s getting booed off the stage every night, as he tours in support of his new comedy album, Very Famous.

But Michael Ian Black is nowhere more self-loathing than in “Sad Sad Conversation”, an ongoing YouTube project, where he and other performers and writers upload homemade videos of themselves talking about the travails of getting by in show business. The other “sadsters” include Josh Malina, Steven Weber, Jane Wiedlin of the Go Go’s, Morgan Murphy, Phil Lamarr, Samm Levine, Steve Agee, Sarah Thyre, Lin-Manuel Miranda, and Jill Morris. The resulting “sadness” is by turns poignant, educational, and of course very funny.

PopMatters talked with Michael Ian Black about everything from his infinite “sadness” to the use of existential obscenity in Very Famous to getting away from his stage persona and into a more honest place with his comedy.

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First off, I have to say I’m a huge fan of ‘Sad Sad Conversation.’

Oh, really? You might be the first person I’ve ever met who is.

I’m kind of obsessed with it actually. I think I’ve watched all of the videos.

I don’t think even I’ve done that.

Did you see that James L. Brooks Tweeted about it the other day?

No, I didn’t. What did he write?

He said something about how it shows that no one should ever date a comedian.

[laughs] I think he’s right.

... so I don’t know if that was the goal or not.

The goal was to further alienate people as much as possible. And I think we’re succeeding.

Even on a career level.

Especially on a career level. And to make ourselves even more unemployable.

But really, I can’t be the only one who enjoys ‘Sad Sad Conversation.’

Honestly, if you look at the views per video, each video only gets like 400-500 views. So it’s a really small amount of people watching it, which is fine. I mean, it’s definitely not for everybody. It’s a pretty specific audience. I think you’d really have to care about, like, what are these people’s personal problems. It’s really just ... people bitching about their lives.

But it was something compelling to me, when we started doing it. [It’s about] this middle class actor thing. There is a ton of stuff out there for really successful showbiz people and for really unsuccessful showbiz people. But there’s not a lot of stuff about people who are just getting by ... or the frustrations with the creative process. And if there’s anything that I think the ‘Sad Sad Conversation’ is totally about, it’s the creative process.

So hopefully it appeals to people other than just shitty actors and shitty comedians. Hopefully anybody who can engage in any kind of creative pursuit can find something in our conversation. You know, is it totally self-aggrandizing? Of course it is.

I was in a panic when I first started it. I just thought, ‘This is just the worst. This is just the worst thing I’ve ever done,’ in terms of being naked and earnest and really letting myself be exposed in that way. And that’s kind of why I made myself keep doing it. Because whenever something feels that uncomfortable, it’s probably worth doing.

And I think you actually talked about that in one of your sad sad videos. About how you want to move into comedy that is less about this ‘Michael Ian Black character’ and into a style that is more honest.

Yeah. Yeah. Unfortunately, I’m much funnier as the fake me than I am as the real me. I wish it wasn’t the case. I wish the real me was just this hilarious jokester. Uh, but I’m not. I’m kind of stoic.

I think that would be great if you did a ‘Sad Sad’ video on stage ... just got up on stage and were just really sad for, like, an hour.

[laughs] I mean, if you paid $25 or whatever to go to the Chuckle Patch in Indianapolis, and you saw that? I think you’d be really fucking pissed off.

Maybe. One of the reasons I like ‘Sad Sad Conversation’ is that a lot of the ‘Sadsters’ didn’t know each other before. And so they’re getting to know each other as the viewers at home are getting to know them, too.

Well, yeah. There’s a couple people on there that I still haven’t met. I have never met Jill Morris, though we’ve communicated online. I’ve never met Lin-Manuel [Miranda]. I think that’s it of the regular contributors. I think I’ve only met Steven Weber once or twice. My relationship with Phil Lamarr is pretty distanced. We see each other once every few years, though I feel like I’ve really gotten to know him now. Jane Wiedlin I think I’ve only met once or twice.

But, yeah. I think I get to know people really well over their Twitter. And so to add this conversational component to it, it makes it much more intimate. I really do feel like I know these people well.

Is your desire to get into a more real type of comedy and away from the “Michael Ian Black character” a result of sad sad conversation?

No, no. I’ve been thinking a lot about this since before sad sad conversation. In fact, I don’t think I would have ever done sad sad if not for being sort of already going through this process, and trying to figure out how to be funny as myself.

And I’m struggling. I mean, I’m really struggling with it. And will continue to. That’s what interests me.
It’s not that interesting to me to continue to do what I’ve already done for however many years. Um, it’s just not that interesting. I get sick of myself. The character of me. It’s like reading the same page over and over again. As I get older, my attention shifts, and my focus changes. So I want to be true to whatever that is…
I think any career pursuit is just figuring out who you are at a given moment. And lots of the time, I don’t have a real answer.

Who are some comics who work in this more honest vein that you really look up to?

Well, there are a lot of them. And they kind of approach it in different ways. One of the guys who really started inspiring me early on is a guy named Mike Birbiglia. He really figured out pretty early on in his career that he wanted to do exactly this, just to figure out a way to be himself on stage. I think he was feeling really frustrated by comedy club acts that he was seeing. And it was all very funny. And it was all very good. But I think he felt sort of stifled and frustrated, and like he wasn’t being as real with people as he could be. And that inspires me. People like Louis C.K., who has been in this territory for a long time ...
I’m reluctant to ... not reluctant. I want to go down that road, but I want to carve my own avenue. And so that’s what I’m doing, or trying to do. And so far, whatever. I don’t know if I’m succeeding. But I also kind of don’t care.

Is not caring part of the honesty?

Yeah, when I say I don’t care, what I mean is that I’m only doing it because I sort of feel compelled to. And so if I have to lose people along the way, then I have to lose people along the way. And that sucks. But I don’t really think I have a choice. So if I say I don’t care, I’m not being glib and saying, “Fuck you if you don’t get it.” I’m not saying that at all. I’m saying, “I’m sorry if you don’t get it, but I have to at least try.”

Yes. Thanks. I was on Marc Maron’s podcast, and he was relentlessly giving me shit about it. And I was like, “Get off my ass. Why do you have to give me shit about everything?” [laughs] I don’t think I used those words exactly. I think he was just trying to goad me. He’s always trying to get my goat.

You two do seem to have an antagonistic relationship.

We do, but it is also a lot of that is just really that we’re ribbing each other. There’s a lot of respect there. A lot of mutual respect. Actually, I take that back. There’s a lot of respect on my end, and not a lot on his end.

Oh, really. That’s good of him to be up front with you like that.

Well, no. He was denying. [laughs] I was making accusations [of his not respecting me], and he was denying them, though not very convincingly.